ISSUE – Nov. 19 | AIRBNB’S AMBITIOUS SECOND ACT WILL TAKE IT WAY BEYOND COUCH-SURFING

Airbnb shook up the hotel business by giving anyone with a spare bed and a mobile phone a way to start a business. Now, it wants to turn us all into tour guides. Later today at Airbnb Open, its annual “festival of hosting,” the company will announce a new product called Airbnb Trips, a portfolio of offbeat excursions developed by freelance hosts. Brian Chesky, the company’s 35-year-old co-founder and C.E.O., spoke exclusively to Vanity Fair about the new initiative, and his ambitions to move Airbnb beyond its couch-surfing origins.

Some nights, Brian Chesky wakes up with his heart pounding. It’s a familiar feeling—one that he’s had since the early days of Airbnb, the online lodging company he co-founded nearly 10 years ago. Back then, his fears were not unlike those that plague most entrepreneurs: he worried about running out of money, building a product no one wanted, his company going bust. There is little danger of that now. Airbnb, worth $30 billion, operates in every place in the world except Iran, Syria, Sudan, Crimea, and North Korea. Roughly 100 million people—including Beyoncé, Kendall Jenner, and Gwyneth Paltrow—have used the site. And Chesky, at 35 years old, is a billionaire and one of the most powerful C.E.O.’s in Silicon Valley.